Dichlorido(6-methyl-2,2′-bipyridine-κ2N,N′)cobalt(II)

Akbarzadeh Torbati, N.; Rezvani, A.R.; Saravani, H.

doi:10.1107/S1600536812041116

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1332

doi:10.1107/S1600536812041116

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Dichlorido(6-methyl-2,2′-bipyridine-κ²N,N′)cobalt(II)

Niloufar Akbarzadeh Torbati,^a ^* Ali Reza Rezvani ^a and Hamideh Saravani ^a

^aDepartment of Chemistry, University of Sistan and Baluchestan, PO Box 98135-674, Zahedan, Iran
^*Correspondence e-mail: n.akbarzadeh@chem.usb.ac.ir

(Received 24 September 2012; accepted 1 October 2012; online 6 October 2012)

In the title compound, [CoCl₂(C₁₁H₁₀N₂)], the Co^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 6-methyl-2,2′-bipyridine ligand and two terminal Cl atoms. Intermolecular C—H⋯Cl hydrogen bonds and π–π stacking interactions between the pyridine rings [centroid–centroid distance = 3.745 (3) Å] are present in the crystal.

Related literature

For related structures, see: Ahmadi et al. (2009 ); Ahmadi, Ebadi et al. (2008 ); Ahmadi, Kalateh et al. (2008 ); Akbarzadeh Torbati et al. (2010a ,b , 2011 ); Amani et al. (2009 ); Kalateh et al. (2010 ); Newkome et al. (1982 ); Onggo et al. (1990 , 2005 ); Shirvan & Haydari Dezfuli (2012 ).

Experimental

Crystal data

[CoCl₂(C₁₁H₁₀N₂)]
M_r = 300.04
Monoclinic, P 2₁ /n
a = 7.4395 (6) Å
b = 9.4723 (8) Å
c = 17.6439 (15) Å
β = 96.131 (7)°
V = 1236.24 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.79 mm⁻¹
T = 298 K
0.20 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.730, T_max = 0.780
7959 measured reflections
3305 independent reflections
2481 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.131
S = 1.12
3305 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N1	2.034 (3)
Co1—N2	2.038 (3)
Co1—Cl1	2.2320 (13)
Co1—Cl2	2.2121 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Cl1ⁱ	0.96	2.78	3.706 (6)	163
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536812041116/hy2591sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041116/hy2591Isup2.hkl

checkCIF report

Comment top

In recent years, we have reported the synthesis and crystal structures of [Co(6,6'-dmbipy)Cl₂], (II) (Akbarzadeh Torbati et al., 2010b), [Co(Ph₂phen)Cl₂], (III) (Akbarzadeh Torbati et al., 2010a) and [Co(biq)Cl₂], (IV) (Akbarzadeh Torbati et al., 2011) (6,6'-dmbipy = 6,6'-dimethyl-2,2'-bipyridine, Ph₂phen = 2,9-dimethyl-1,10-phenanthroline, biq = 2,2'-biquinoline). 6-Methyl-2,2'-bipyridine (6-mbipy) is a good ligand and a few complexes with 6-mbipy have been prepared, such as that of [Hg(6-mbipy)Cl₂], (V) (Ahmadi, Ebadi et al., 2008), [Pt(6-mbipy)Cl₄], (VI) (Amani et al., 2009), [Pb₄(NO₃)₈(6-mbipy)₄], (VII) (Ahmadi et al., 2009), [Zn(6-mbipy)Br₂], (VIII) (Kalateh et al., 2010), [Zn(6-mbipy)Cl₂], (IX) (Ahmadi, Kalateh et al., 2008), [Pd(6-mbipy)Cl₂], (X) (Newkome et al., 1982), [Ru(6-mbipy)₃][BF₄]₂, (XI) (Onggo et al., 2005), [Fe(6-mbipy)₃][ClO₄]₂.6-mbipy, (XII) (Onggo et al., 1990) and [Cd(6-mbipy)Br₂(DMSO)], (XIII) (Shirvan & Haydari Dezfuli, 2012). We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound (Fig. 1), the Co^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 6-methyl-2,2'-bipyridine ligand and two terminal Cl atoms (Table 1). In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the pyridine rings, Cg2···Cg3ⁱ [centroid–centroid distance = 3.745 (3) Å, symmetry code: (i) 2-x, 2-y, -z, Cg2 and Cg3 are the centroids of the N1/C2–C6 ring and N2/C7–C11 ring, respectively], stabilize the structure.

Related literature top

For related structures, see: Ahmadi et al. (2009); Ahmadi, Ebadi et al. (2008); Ahmadi, Kalateh et al. (2008); Akbarzadeh Torbati et al. (2010a,b, 2011); Amani et al. (2009); Kalateh et al. (2010); Newkome et al. (1982); Onggo et al. (1990, 2005); Shirvan & Haydari Dezfuli (2012).

Experimental top

For the preparation of the title compound, a solution of 6-methyl-2,2'-bipyridine (0.23 g, 1.34 mmol) in methanol (15 ml) was added to a solution of CoCl₂.6H₂O (0.37 g, 1.34 mmol) in acetonitrile (15 ml) and the resulting blue solution was stirred for 15 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, blue block crystals of the title compound were isolated (yield: 0.30 g, 74.6%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Dichlorido(6-methyl-2,2'-bipyridine-κ²N,N')cobalt(II) top

Crystal data top

[CoCl₂(C₁₁H₁₀N₂)]	F(000) = 604
M_r = 300.04	D_x = 1.612 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 998 reflections
a = 7.4395 (6) Å	θ = 2.3–29.3°
b = 9.4723 (8) Å	µ = 1.79 mm⁻¹
c = 17.6439 (15) Å	T = 298 K
β = 96.131 (7)°	Block, blue
V = 1236.24 (18) Å³	0.20 × 0.15 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3305 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 29.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.730, T_max = 0.780	k = −11→12
7959 measured reflections	l = −24→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0444P)² + 1.4058P] where P = (F_o² + 2F_c²)/3
3305 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[CoCl₂(C₁₁H₁₀N₂)]	V = 1236.24 (18) Å³
M_r = 300.04	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4395 (6) Å	µ = 1.79 mm⁻¹
b = 9.4723 (8) Å	T = 298 K
c = 17.6439 (15) Å	0.20 × 0.15 × 0.14 mm
β = 96.131 (7)°

Data collection top

Bruker APEXII CCD diffractometer	3305 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2481 reflections with I > 2σ(I)
T_min = 0.730, T_max = 0.780	R_int = 0.043
7959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.12	Δρ_max = 0.85 e Å⁻³
3305 reflections	Δρ_min = −0.48 e Å⁻³
145 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6700 (9)	0.9546 (6)	0.2127 (3)	0.0841 (16)
H1A	0.7822	0.9086	0.2296	0.101*
H1B	0.5749	0.8858	0.2064	0.101*
H1C	0.6430	1.0233	0.2498	0.101*
C2	0.6857 (6)	1.0262 (5)	0.1385 (3)	0.0549 (10)
C3	0.6639 (6)	1.1710 (5)	0.1282 (3)	0.0661 (12)
H3	0.6359	1.2279	0.1683	0.079*
C4	0.6843 (7)	1.2286 (5)	0.0589 (3)	0.0679 (13)
H4	0.6706	1.3254	0.0518	0.081*
C5	0.7246 (6)	1.1457 (4)	−0.0005 (3)	0.0572 (10)
H5	0.7389	1.1850	−0.0478	0.069*
C6	0.7439 (4)	1.0016 (4)	0.0116 (2)	0.0430 (8)
C7	0.7826 (5)	0.8999 (4)	−0.0480 (2)	0.0446 (8)
C8	0.8106 (6)	0.9397 (5)	−0.1220 (2)	0.0582 (11)
H8	0.8110	1.0345	−0.1357	0.070*
C9	0.8380 (7)	0.8356 (6)	−0.1748 (3)	0.0686 (13)
H9	0.8574	0.8599	−0.2243	0.082*
C10	0.8363 (7)	0.6973 (6)	−0.1535 (3)	0.0703 (13)
H10	0.8512	0.6264	−0.1888	0.084*
C11	0.8125 (6)	0.6635 (5)	−0.0799 (3)	0.0601 (11)
H11	0.8138	0.5690	−0.0656	0.072*
N1	0.7245 (4)	0.9445 (3)	0.08066 (17)	0.0431 (7)
N2	0.7872 (4)	0.7629 (3)	−0.02746 (18)	0.0465 (7)
Co1	0.76711 (7)	0.73253 (5)	0.08569 (3)	0.04458 (16)
Cl1	1.03449 (15)	0.68766 (14)	0.15119 (7)	0.0683 (3)
Cl2	0.54399 (16)	0.59698 (13)	0.11655 (7)	0.0673 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.114 (5)	0.085 (4)	0.056 (3)	0.010 (3)	0.024 (3)	−0.014 (3)
C2	0.049 (2)	0.055 (2)	0.061 (2)	0.0011 (18)	0.0059 (18)	−0.0083 (19)
C3	0.056 (2)	0.061 (3)	0.081 (3)	0.005 (2)	0.005 (2)	−0.021 (2)
C4	0.060 (3)	0.040 (2)	0.103 (4)	−0.0006 (19)	0.004 (3)	0.003 (2)
C5	0.052 (2)	0.046 (2)	0.073 (3)	−0.0005 (17)	0.003 (2)	0.013 (2)
C6	0.0343 (16)	0.0436 (18)	0.050 (2)	−0.0035 (14)	0.0007 (14)	0.0110 (15)
C7	0.0353 (16)	0.050 (2)	0.048 (2)	−0.0082 (15)	0.0024 (14)	0.0068 (16)
C8	0.054 (2)	0.070 (3)	0.049 (2)	−0.012 (2)	0.0021 (18)	0.018 (2)
C9	0.066 (3)	0.102 (4)	0.039 (2)	−0.010 (3)	0.0119 (19)	0.003 (2)
C10	0.073 (3)	0.090 (4)	0.050 (3)	−0.005 (3)	0.015 (2)	−0.015 (2)
C11	0.061 (2)	0.063 (3)	0.057 (3)	−0.003 (2)	0.012 (2)	−0.009 (2)
N1	0.0412 (15)	0.0412 (15)	0.0465 (17)	0.0016 (12)	0.0027 (13)	0.0022 (13)
N2	0.0442 (15)	0.0499 (17)	0.0458 (16)	−0.0021 (13)	0.0070 (13)	0.0040 (14)
Co1	0.0474 (3)	0.0416 (3)	0.0458 (3)	0.0009 (2)	0.0098 (2)	0.0099 (2)
Cl1	0.0500 (5)	0.0788 (8)	0.0754 (7)	0.0019 (5)	0.0033 (5)	0.0350 (6)
Cl2	0.0590 (6)	0.0654 (7)	0.0786 (8)	−0.0129 (5)	0.0130 (5)	0.0186 (6)

Geometric parameters (Å, º) top

C1—C2	1.490 (7)	C7—N2	1.346 (5)
C1—H1A	0.9600	C7—C8	1.397 (5)
C1—H1B	0.9600	C8—C9	1.386 (7)
C1—H1C	0.9600	C8—H8	0.9300
C2—N1	1.336 (5)	C9—C10	1.363 (8)
C2—C3	1.391 (6)	C9—H9	0.9300
C3—C4	1.363 (7)	C10—C11	1.367 (6)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.368 (7)	C11—N2	1.347 (5)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.386 (5)	Co1—N1	2.034 (3)
C5—H5	0.9300	Co1—N2	2.038 (3)
C6—N1	1.355 (5)	Co1—Cl1	2.2320 (13)
C6—C7	1.477 (5)	Co1—Cl2	2.2121 (11)

C2—C1—H1A	109.5	C9—C8—C7	118.9 (4)
C2—C1—H1B	109.5	C9—C8—H8	120.6
H1A—C1—H1B	109.5	C7—C8—H8	120.6
C2—C1—H1C	109.5	C10—C9—C8	119.5 (4)
H1A—C1—H1C	109.5	C10—C9—H9	120.2
H1B—C1—H1C	109.5	C8—C9—H9	120.2
N1—C2—C3	120.2 (4)	C9—C10—C11	119.5 (5)
N1—C2—C1	116.8 (4)	C9—C10—H10	120.3
C3—C2—C1	122.9 (4)	C11—C10—H10	120.3
C4—C3—C2	119.3 (4)	N2—C11—C10	122.1 (5)
C4—C3—H3	120.4	N2—C11—H11	119.0
C2—C3—H3	120.4	C10—C11—H11	119.0
C3—C4—C5	120.8 (4)	C2—N1—C6	120.6 (3)
C3—C4—H4	119.6	C2—N1—Co1	125.7 (3)
C5—C4—H4	119.6	C6—N1—Co1	113.7 (2)
C4—C5—C6	118.4 (4)	C7—N2—C11	119.3 (3)
C4—C5—H5	120.8	C7—N2—Co1	113.4 (3)
C6—C5—H5	120.8	C11—N2—Co1	127.2 (3)
N1—C6—C5	120.7 (4)	N1—Co1—N2	81.08 (13)
N1—C6—C7	115.3 (3)	N1—Co1—Cl2	117.79 (9)
C5—C6—C7	123.9 (4)	N2—Co1—Cl2	117.29 (10)
N2—C7—C8	120.7 (4)	N1—Co1—Cl1	109.69 (10)
N2—C7—C6	116.0 (3)	N2—Co1—Cl1	112.31 (10)
C8—C7—C6	123.3 (4)	Cl2—Co1—Cl1	114.38 (5)

N1—C2—C3—C4	−0.6 (7)	C5—C6—N1—Co1	−178.0 (3)
C1—C2—C3—C4	178.6 (5)	C7—C6—N1—Co1	3.0 (4)
C2—C3—C4—C5	0.4 (7)	C8—C7—N2—C11	−2.5 (6)
C3—C4—C5—C6	0.2 (7)	C6—C7—N2—C11	176.6 (3)
C4—C5—C6—N1	−0.5 (6)	C8—C7—N2—Co1	174.3 (3)
C4—C5—C6—C7	178.4 (4)	C6—C7—N2—Co1	−6.6 (4)
N1—C6—C7—N2	2.4 (5)	C10—C11—N2—C7	0.9 (7)
C5—C6—C7—N2	−176.5 (4)	C10—C11—N2—Co1	−175.4 (4)
N1—C6—C7—C8	−178.5 (3)	C2—N1—Co1—N2	176.8 (3)
C5—C6—C7—C8	2.6 (6)	C6—N1—Co1—N2	−5.0 (2)
N2—C7—C8—C9	1.9 (6)	C2—N1—Co1—Cl2	60.6 (3)
C6—C7—C8—C9	−177.1 (4)	C6—N1—Co1—Cl2	−121.3 (2)
C7—C8—C9—C10	0.2 (7)	C2—N1—Co1—Cl1	−72.6 (3)
C8—C9—C10—C11	−1.8 (8)	C6—N1—Co1—Cl1	105.6 (2)
C9—C10—C11—N2	1.2 (8)	C7—N2—Co1—N1	6.3 (3)
C3—C2—N1—C6	0.3 (6)	C11—N2—Co1—N1	−177.1 (4)
C1—C2—N1—C6	−178.9 (4)	C7—N2—Co1—Cl2	123.1 (2)
C3—C2—N1—Co1	178.3 (3)	C11—N2—Co1—Cl2	−60.4 (4)
C1—C2—N1—Co1	−0.9 (6)	C7—N2—Co1—Cl1	−101.4 (3)
C5—C6—N1—C2	0.3 (5)	C11—N2—Co1—Cl1	75.2 (4)
C7—C6—N1—C2	−178.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Cl1ⁱ	0.96	2.78	3.706 (6)	163

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[CoCl₂(C₁₁H₁₀N₂)]
M_r	300.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.4395 (6), 9.4723 (8), 17.6439 (15)
β (°)	96.131 (7)
V (Å³)	1236.24 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.79
Crystal size (mm)	0.20 × 0.15 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.730, 0.780
No. of measured, independent and observed [I > 2σ(I)] reflections	7959, 3305, 2481
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.131, 1.12
No. of reflections	3305
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.48

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—N1	2.034 (3)	Co1—Cl1	2.2320 (13)
Co1—N2	2.038 (3)	Co1—Cl2	2.2121 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Cl1ⁱ	0.96	2.78	3.706 (6)	163

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

We are grateful to the University of Sistan and Baluchestan and Shahid Beheshti University for financial support.

References

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